CN115141214B - Near infrared organic micromolecule BBTD-TP with multiple rotors, nano particles and application thereof - Google Patents
Near infrared organic micromolecule BBTD-TP with multiple rotors, nano particles and application thereof Download PDFInfo
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- 238000005481 NMR spectroscopy Methods 0.000 description 6
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- DEGAKNSWVGKMLS-UHFFFAOYSA-N calcein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(O)=O)CC(O)=O)=C(O)C=C1OC1=C2C=C(CN(CC(O)=O)CC(=O)O)C(O)=C1 DEGAKNSWVGKMLS-UHFFFAOYSA-N 0.000 description 1
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- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
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- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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Abstract
The invention discloses a near infrared organic micromolecule BBTD-TP with multiple rotors, and nano particles and application thereof. The near infrared organic micromolecule BBTD-TP with multiple rotors is dissolved in an organic solvent, slowly added into an aqueous solution containing amphiphilic copolymer in a dropwise manner under an ultrasonic environment, stirred for a period of time, and treated to obtain nano particles BBTD-TP NPs. The nanoparticle BBTD-TP NPs are used as photothermal agents in biological imaging and treatment. The nanoparticle has the capability of near infrared two-region absorption, excellent photo-thermal conversion capability and fluorescence emission capability, and has good biocompatibility and strong phototoxicity in vitro.
Description
Technical Field
The invention belongs to the field of pharmaceutical preparations, and relates to a near infrared organic micromolecule BBTD-TP with multiple rotors, nanoparticles and application thereof.
Background
Over the past several decades, with the rapid development of technology, many new cancer treatments have emerged, such as immunotherapy, gene therapy, photodynamic therapy, photothermal therapy, and the like. The photothermal treatment is to inject a material (photothermal reagent) with high photothermal conversion efficiency into a living body, the photothermal reagent is specifically gathered at a tumor part by utilizing a targeting identification technology or high permeability and retention effect of solid tumors, and the absorbed light energy is converted into heat energy after the tumor part is irradiated by laser. The heat can fully increase the temperature of the tumor, so that irreversible cell damage is caused, and the advantages of high efficiency, short treatment time, controllable radiation and temperature and the like are achieved. Moreover, biological imaging, such as photoacoustic imaging and photothermal imaging, can be performed simultaneously in this process. Photo-thermal treatment is conducted under the guidance of photo-acoustic/photo-thermal imaging, so that synchronous and accurate tumor imaging can be provided and tumors can be eliminated only by one injection and single irradiation.
The light in photothermal therapy is different from the common visible light, and near infrared light is used. The near infrared light has deeper tissue penetration and a low fluorescence background for organisms than visible light, and has less side effects than conventional X-rays. At present, the research on infrared light is more prone to using light in a near infrared two-region, and the light of NIR-II has longer emission wavelength compared with NIR-I, so that the scattering and absorption of photons in biological tissues can be remarkably reduced, the time and spatial resolution are higher, and the penetrating power is stronger.
The photothermal agent has no toxicity under dark conditions and has toxicity under illumination conditions, and compared with the traditional chemotherapy and radiotherapy, the photothermal agent has good space specificity and non-invasive performance, and meets the requirements of the current biomedical field on treatment. Current near infrared photothermal agents include organic small molecule materials, semiconducting polymer nanomaterials, carbon nanomaterials, metallic nanomaterials, etc., which generally have better biocompatibility, especially higher body clearance, than inorganic and polymeric materials.
Disclosure of Invention
The invention aims at overcoming the defects of the prior art and providing a near infrared small organic molecule BBTD-TP with multiple rotors.
The chemical structural formula of the near infrared organic micromolecule BBTD-TP with multiple rotors is as follows:
the second object of the invention is to provide a synthesis method of the near infrared small organic molecule BBTD-TP with multiple rotors; the synthetic route is as follows:
the synthesis method comprises the following steps:
(1) Dissolving the compound 1 in an ultra-dry tetrahydrofuran solution under the protection of argon, and then adding a halogenating agent in an ice water bath for a small amount for multiple times under the condition of avoiding light; reacting for 1.5-3 hours, and obtaining a compound 2 through post-treatment;
preferably, the ratio of the amounts of the substances of the compound 1 and the halogenating agent is 1:5, a step of;
preferably, the halogenating agent is one or more of N-bromosuccinimide, liquid bromine, potassium bromate, bromine water, iodic acid, halogen and N-chlorosuccinimide, more preferably N-bromosuccinimide;
(2) Dissolving a compound 2, 1- (4-phenylboronic acid pinacol ester) -1, 2-tristyrene, an acid binding agent and a catalyst in a mixed solvent of tetrahydrofuran and water, then freezing and pumping with liquid nitrogen and nitrogen for three times to deoxidize, and heating and reacting for 12-24 hours at 75-80 ℃ under the protection of argon; after the reaction is finished, obtaining a compound BBTD-TP through post-treatment;
preferably, the ratio of the amounts of the substances of the compound 2, 4-vinylphenylboronic acid, potassium carbonate and catalyst is 1: 6-8: 8:0.04;
preferably, the catalyst adopts one or more of tetra (triphenylphosphine) palladium, palladium acetate, triphenylphosphine and 1,1' -bis-diphenylphosphine ferrocene palladium dichloride, and more preferably tetra (triphenylphosphine) palladium;
preferably, the acid binding agent adopts one or more of potassium carbonate, cesium carbonate and triethylamine, and more preferably potassium carbonate;
preferably, in the step (1), the post-treatment method comprises the following steps: after the tetrahydrofuran solvent is removed from the reactant, the reactant is extracted by dichloromethane and water, an organic phase is collected, and a crude product is obtained after drying and filtering, and then the volume ratio of petroleum ether to dichloromethane is 5: and (3) taking the mixed solution of 1 as an eluent, and separating and purifying by a silica gel chromatographic column to obtain the compound 2.
Preferably, in the step (2), the post-treatment method comprises the following steps: the reaction product is extracted by dichloromethane and water, an organic phase is collected, and a crude product is obtained after drying and filtering, and then the volume ratio of petroleum ether to dichloromethane is 3: and (3) taking the mixed solution of 1 as an eluent, and separating and purifying by a silica gel chromatographic column to obtain the compound BBTD-TP.
A third object of the present invention is to provide the above water-soluble nanoparticle of near infrared small organic molecules BBTD-TP with multiple rotors; the synthesis method comprises the following steps:
dissolving near infrared organic micromolecule BBTD-TP with multiple rotors in an organic solvent, slowly dropwise adding the organic micromolecule BBTD-TP into an aqueous solution containing an amphiphilic copolymer in an ultrasonic environment, stirring for a period of time, and treating to obtain nano-particle BBTD-TP NPs.
The amphiphilic polymer adopts DSPE-PEG 2000 、DSPE-PEG 2000 -OH、DSPE-PEG 2000 -COOH、DSPE-PEG 2000 -NH 3 One or more of (a) and (b).
Specifically, BBTD-TP is dissolved in tetrahydrofuran solution to obtain BBTD-TP solution; DSPE-PEG 2000 Dissolving in water to obtain DSPE-PEG 2000 A solution; slowly dripping BBTD-TP solution into DSPE-PEG under ultrasonic environment 2000 The solution was stirred at room temperature for 24 hours with aeration; after passing through a 0.22 μm aqueous filter, the mixture was frozen and concentrated to a solid powder under low temperature and low pressure conditions.
The compounds BBTD-TP and DSPE-PEG 2000 The mass ratio of (2) is 1:5 to 10.
The fourth object of the invention is to provide the application of the water-soluble nano particles of the near infrared small organic molecules BBTD-TP with multiple rotors as a photothermal agent in biological imaging and treatment.
The beneficial effects of the invention are as follows:
the invention designs and synthesizes the near infrared organic micromolecule BBTD-TP with multiple rotors by balancing the energy decay path between the radiation decay and the non-radiation decay.
The invention provides application of nanoparticles prepared by near infrared small organic molecules BBTD-TP with multiple rotors as a photothermal agent in biological imaging and treatment. The nanoparticle has the capability of near infrared two-region absorption, excellent photo-thermal conversion capability and fluorescence emission capability. In vitro experiments, the composition shows good biocompatibility and strong phototoxicity.
Drawings
FIG. 1 is a chart showing the nuclear magnetic resonance hydrogen spectrum of compound 2 synthesized in example one (deuterated chloroform as solvent);
FIG. 2 is a chart of nuclear magnetic resonance spectroscopy (deuterated chloroform as solvent) of compound 2 synthesized in example one;
FIG. 3 is a high resolution mass spectrum of compound 2 synthesized in example one;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of the compound BBTD-TP synthesized in example one (deuterated chloroform as solvent);
FIG. 5 is a chart of nuclear magnetic resonance spectroscopy (deuterated chloroform as solvent) of the compound BBTD-TP synthesized in example one;
FIG. 6 is a high resolution mass spectrum of compound BBTD-TP synthesized in example one;
FIG. 7 is an in vitro photo-thermal property of the nanoparticle; wherein (a) is a temperature change graph of BBTD-TP NPs aqueous solution under different intensity lasers, (b) is a temperature change graph of nano particles with different concentrations under laser irradiation, (c) is a photo-thermal imaging graph of BBTD-TP NPs aqueous solution under different intensity lasers, and (d) is a temperature change of 4 irradiation-cooling cycles under the laser conditions.
FIG. 8 shows the in vitro photothermal therapeutic effect of the nanoparticles (B16F 10 cells); wherein (a) is the cell viability after co-incubation with different concentrations of BBTD-TP NPs and (b) is the live/dead staining image of different cells after different treatments.
Detailed Description
As described above, in view of the shortcomings of the prior art, the present inventors have long studied and practiced in a large number of ways, and have proposed the technical solution of the present invention, which is based on at least: (1) Introducing a tetrastyrene group into the molecule to obtain red-shifted absorption and improved photo-thermal conversion efficiency; (2) The nano particles obtained by wrapping the obtained molecules with amphiphilic polymers are used as a multifunctional nano platform, and can be absorbed in a near infrared two-region, high-efficiency photo-thermal conversion efficiency, good fluorescence emission and excellent light stability through reasonable molecular design, and can be applied to biological tumor imaging and treatment.
The present invention will be described in further detail with reference to the drawings and examples, in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention. In addition, the technical features of the embodiments of the present invention described below may be combined with each other as long as they do not collide with each other.
In a first aspect, there is provided a near infrared small organic molecule BBTD-TP with multiple rotors, the synthetic route of which is:
(1) Dissolving the compound 1 in an ultra-dry tetrahydrofuran solution under the protection of argon, and then adding a halogenating agent in an ice water bath for a small amount for multiple times under the condition of avoiding light; reacting for 1.5-3 hours, and obtaining a compound 2 through post-treatment;
the ratio of the amounts of the substances of the compound 1 and the halogenating agent is 1:5, a step of;
the halogenating agent adopts one or more of N-bromosuccinimide, liquid bromine, potassium bromate, bromine water, iodic acid, halogen and N-chlorosuccinimide.
(2) Dissolving a compound 2, 1- (4-phenylboronic acid pinacol ester) -1, 2-tristyrene, an acid binding agent and a catalyst in a mixed solvent of tetrahydrofuran and water, then freezing and pumping with liquid nitrogen and nitrogen for three times to remove oxygen, and heating and reacting for 12-24 hours at 75-80 ℃ under the protection of argon; after the reaction is finished, obtaining a compound BBTD-TP through post-treatment;
the ratio of the amounts of the substances of the compound 2, the 1- (4-phenylboronic acid pinacol ester) -1, 2-triphenylethylene, the acid binding agent and the catalyst is 1: 6-8: 8:0.04;
the catalyst adopts one or more of tetra (triphenylphosphine) palladium, palladium acetate, triphenylphosphine and 1,1' -bis (diphenylphosphine) ferrocene palladium dichloride;
the acid binding agent adopts one or more of potassium carbonate, cesium carbonate and triethylamine.
Preferably, in the step (1), the post-treatment method comprises the following steps: after the tetrahydrofuran solvent is removed from the reactant, the reactant is extracted by dichloromethane and water, an organic phase is collected, and a crude product is obtained after drying and filtering, and then the volume ratio of petroleum ether to dichloromethane is 5: and (3) taking the mixed solution of 1 as an eluent, and separating and purifying by a silica gel chromatographic column to obtain the compound 2.
Preferably, in the step (2), the post-treatment method comprises the following steps: the reaction product is extracted by dichloromethane and water, an organic phase is collected, and a crude product is obtained after drying and filtering, and then the volume ratio of petroleum ether to dichloromethane is 3: and (3) taking the mixed solution of 1 as an eluent, and separating and purifying by a silica gel chromatographic column to obtain the compound BBTD-TP.
In a second aspect, there is provided a water-soluble nanoparticle of near infrared small organic molecules BBTD-TP having multiple rotors, synthesized by:
dissolving near infrared organic micromolecule BBTD-TP with multiple rotors in an organic solvent, slowly dropwise adding the organic micromolecule BBTD-TP into an aqueous solution containing an amphiphilic copolymer in an ultrasonic environment, stirring for a period of time, and treating to obtain nano-particle BBTD-TP NPs.
The following description of the present invention is further provided with reference to several preferred embodiments, but the experimental conditions and setting parameters should not be construed as limiting the basic technical scheme of the present invention. And the scope of the present invention is not limited to the following examples.
Embodiment one: preparation of near infrared organic small molecule BBTD-TP with multiple rotors
Step (1) -preparation of compound 2:
compound 1 (30 mg,0.02 mmol) was added to a 25mL round bottom flask under argon and dissolved by adding ultra-dry tetrahydrofuran (10 mL). N-bromosuccinimide (17.6 g,0.1 mmol) was added slowly in portions under ice-water bath conditions and reacted at 0℃for 1.5 hours under argon atmosphere. Reaction completionAfter that, the solvent was removed by a rotary evaporator. Extraction with dichloromethane and water and collection of the organic phase over MgSO 4 Drying, filtration and concentration under reduced pressure using a rotary evaporator gave a crude product which was purified by column chromatography on silica gel (petroleum ether/dichloromethane, v/v, 5:1) to finally give a green solid (18 mg, 49.7%), melting point: 80-82 ℃.
As shown in fig. 1-3: 1 HNMR(500MHz,CDCl 3 ,298K)δ(ppm):8.86(s,2H),7.49(d,J＝8.5Hz,4H),7.40(d,J＝8.7Hz,8H),7.11(d,J＝8.5Hz,4H),7.01(d,J＝8.8Hz,8H),2.77(d,J＝7.0Hz,4H),1.78(m,2H),1.29-1.20(m,80H),0.86(m,12H). 13 C NMR(126MHz,CDCl 3 ,298K)δ(ppm):151.0,146.3,146.2,144.1,138.8,136.2,135.5,132.5,130.3,129.7,125.8,123.6,116.0,112.8,39.1,33.5,33.2,31.9,30.1,29.8,29.8,29.7,29.7,29.7,29.7,29.4,29.4,26.5,22.7,14.1.ESI-HRMS[2+H] + :calcd.for[C 98 H 134 Br 4 N 6 S 4 ] + 1829.5474,found 1829.5474.
step (2) -preparation of compound BBTD-TP:
compound 2 (144 mg,0.0785 mmol), 1- (4-phenylboronic acid pinacol ester) -1, 2-tristyrene (0.55 mmol), potassium carbonate (87 mg, 0.6278 mmol), tetrakis (triphenylphosphine) palladium (3.6 mg,0.0031 mmol) were placed in a 50mL Shi Laike bottle, a mixed solvent of tetrahydrofuran and water was added to dissolve the solid (tetrahydrofuran/water, v/v, 3:2), and then the mixture was frozen with liquid nitrogen and nitrogen for 3 times to remove oxygen. The reaction was heated at 75℃for 18 hours under the protection of argon atmosphere. After the reaction was completed, it was cooled to room temperature and concentrated under reduced pressure using a rotary evaporator. Extraction with dichloromethane and water and collection of the organic phase over MgSO 4 Drying, filtration and concentration under reduced pressure using a rotary evaporator gave a crude product which was purified by column chromatography on silica gel (petroleum ether/dichloromethane, v/v, 3:1) to give finally a green solid (65 mg, 29.2%), melting point: M.P.147 ℃.
Shown in FIGS. 4-6 1 HNMR(500MHz,CDCl 3 ,298K)δ(ppm):8.89(s,2H),7.51(d,J＝8.6Hz,12H),7.37(d,J＝8.3Hz,8H),7.20(dd,J＝8.5,7.8Hz,12H),7.15-7.04(m,68H),2.81(d,J＝6.3Hz,4H),1.82(m,2H),1.32-1.17(m,80H),1.02-0.70(m,12H). 13 C NMR(126MHz,CDCl 3 ,298K)δ(ppm):151.2,147.0,146.5,144.6,143.8,143.7,142.5,141.0,140.6,138.8,138.1,136.2,135.4,135.3,131.8,131.4,131.3,130.1,128.9,127.7,127.7,127.6,126.5,126.4,125.7,124.7,123.3,113.0,39.1,33.5,33.2,31.9,30.1,29.8,29.7,29.7,29.7,29.7,29.6,29.4,29.3,26.5,22.7,14.1.ESI-HRMS[BBTD-TP+H] + :calcd.for[C 202 H 201 N 6 S 4 ] + 2838.479,found 2838.4725.
Embodiment two: preparation of BBTD-TP nanoparticles
Dissolving 0.5mgBBTD-TP in 2mL tetrahydrofuran to obtain BBTD-TP solution; 5mgDSPE-PEG 2000 Dissolving in 10mL of water to obtain DSPE-PEG 2000 A solution; slowly dripping BBTD-TP solution into DSPE-PEG under ultrasonic environment 2000 The solution was stirred at room temperature for 24 hours with aeration; after passing through a 0.22 μm aqueous filter, the mixture was frozen and concentrated to a solid powder under low temperature and low pressure conditions.
Embodiment four: in vitro photo-thermal properties of said nanoparticles
Placing 1mL of the two nanoparticle solution in a centrifuge tube with 1.5mL, and irradiating the nanoparticle aqueous solutions with different concentrations by laser with the power density of 1.0W/cm 2 Photothermal images and temperatures of the solutions were recorded. The same concentration of nanoparticle aqueous solution (30. Mu.M) was irradiated with different power lasers and the photothermal image and temperature of the solution were recorded. The aqueous nanoparticle solution (30. Mu.M) was irradiated with a laser and the temperature change of the solution over 4 radiation cooling cycles was measured to detect photostability.
As shown in fig. 7: the temperature rise of the solution was observed to be positively correlated with laser power and concentration and to exhibit good photostability.
Fifth embodiment: in vitro photothermal therapeutic effect of said nanoparticles
The MTT method was used to evaluate the cytotoxicity and photothermal effect of the example two nanoparticles in vitro. B16F10 cells were seeded in 96-well plates (104 cells per well) and incubated for 18h. Fresh medium containing different concentrations of example two nanoparticles (0, 0.1, 0.2, 0.4, 0.8, 1.0 and 2.0 μm) was then changed in each well. After 24 hours, use laser(1.5W/cm 2 ) The cells were irradiated for 5min. After stabilization for 18h, the medium was replaced with MTT solution (0.5 mg/mL) at 100. Mu.L per well. Then incubate in the dark for another 4h. Finally, MTT medium was removed and formazan crystals formed were dissolved in DMSO (100. Mu.L). Absorbance at 570nm was monitored using a microplate reader. Cell viability was calculated from absorbance. In addition, live and dead cell staining was used to intuitively demonstrate the in vitro photothermal therapeutic effect of the nanoparticles, and B16F10 cells were seeded in 24-well plates (10 per well 4 Individual cells), for 18h. The cells were then treated with the following treatments: a control; control + laser irradiation; only nanoparticles; nanoparticle + laser irradiation. After 18h, the nanoparticle-containing medium was removed, the cells were washed 2 times with physiological saline and stained with calcein/propidium iodide for 30min. After washing twice with physiological saline, live cells (green) and dead cells (red) were imaged with an inverted fluorescence microscope.
As shown in fig. 8: with increasing nanoparticle concentration, cell viability exceeded 80% under laser irradiation. The effect on cell survival was negligible with nanoparticle treatment and no laser irradiation, indicating good biocompatibility and excellent cell killing ability of the nanoparticles.
Claims (9)
1. The near infrared organic micromolecule BBTD-TP with multiple rotors is characterized by having the following chemical structural formula:
2. a synthesis method of near infrared organic micromolecule BBTD-TP with multiple rotors; the method is characterized by comprising the following steps:
(1) Dissolving the compound 1 in ultra-dry tetrahydrofuran THF solution under the protection of argon, then adding a halogenating agent N-bromosuccinimide NBS into an ice water bath to react for 1.5-3 hours under the condition of avoiding light, and obtaining a compound 2 through post-treatment;
(2) The compound 2, 1- (4-phenylboronic acid pinacol ester) -1, 2-triphenylethylene and the catalyst Pd (PPh) 3 ) 4 Acid binding agent K 2 CO 3 Dissolving in a mixed solvent of tetrahydrofuran THF and water, freezing and pumping with liquid nitrogen and nitrogen for three times to deoxidize, and heating and reacting for 12-24 hours at 75 ℃ under the protection of argon; after the reaction is finished, the compound BBTD-TP is obtained through post-treatment.
3. The process according to claim 2, characterized in that the ratio of the amounts of substances of compound 1, N-bromosuccinimide is 1:5, a step of; compound 2, 1- (4-phenylboronic acid pinacol ester) -1, 2-triphenylethylene, K 2 CO 3 、Pd(PPh 3 ) 4 The ratio of the amounts of the substances is 1: (6-8): 8:0.04.
4. the method according to claim 2, wherein in step (1), the post-treatment method is as follows: after the tetrahydrofuran solvent is removed from the reactant, the reactant is extracted by dichloromethane and water, an organic phase is collected, and a crude product is obtained after drying and filtering, and then the volume ratio of petroleum ether to dichloromethane is 5: and (3) taking the mixed solution of 1 as an eluent, and separating and purifying by a silica gel chromatographic column to obtain the compound 2.
5. The method according to claim 2, wherein in step (2), the post-treatment method is as follows: the reaction product is extracted by dichloromethane and water, an organic phase is collected, and a crude product is obtained after drying and filtering, and then the volume ratio of petroleum ether to dichloromethane is 3: and (3) taking the mixed solution of 1 as an eluent, and separating and purifying by a silica gel chromatographic column to obtain the compound BBTD-TP.
6. The synthesis method of the water-soluble nano particles of the near infrared organic micromolecule BBTD-TP with multiple rotors is characterized by comprising the following steps:
dissolving the near infrared small organic molecule BBTD-TP with multiple rotors in an organic solvent, slowly dropwise adding the solution into an aqueous solution containing an amphiphilic copolymer in an ultrasonic environment, stirring for a period of time, and treating to obtain nano particles BBTD-TP NPs;
the amphiphilic polymer adopts DSPE-PEG 2000 、DSPE-PEG 2000 -OH、DSPE-PEG 2000 -COOH、DSPE-PEG 2000 -NH 3 One or more of (a) and (b).
7. The method according to claim 6, wherein the BBTD-TP solution is obtained by dissolving BBTD-TP in a tetrahydrofuran solution; DSPE-PEG 2000 Dissolving in water to obtain DSPE-PEG 2000 A solution; slowly dripping BBTD-TP solution into DSPE-PEG under ultrasonic environment 2000 The solution was stirred at room temperature for 24 hours with aeration; freezing after passing through 0.22 μm water filter, concentrating under low temperature and low pressure to obtain solid powder;
the compounds BBTD-TP and DSPE-PEG 2000 The mass ratio of (2) is 1:5 to 10.
8. A water-soluble nanoparticle synthesized by the method of claim 6 or 7.
9. A use of a water-soluble nanoparticle according to claim 8 as a photothermal agent in therapy.
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